Rollingwood Homes for Sale

Rollingwood Homes for Sale

Welcome to Rollingwood, a picturesque subdivision that epitomizes the charm and tranquility of suburban living in the heart of the United States. Nestled amidst lush greenery and serene landscapes, Rollingwood offers a perfect blend of comfort, convenience, and community spirit, making it an ideal place for families, professionals, and retirees alike.

As you explore Rollingwood, you'll discover a variety of homes for sale that cater to diverse tastes and lifestyles. From cozy single-family residences to spacious modern designs, each property boasts unique features and thoughtful layouts. Many homes in this charming neighborhood come with beautifully landscaped yards, inviting outdoor spaces, and state-of-the-art amenities, ensuring that you find the perfect sanctuary to call your own.

The community thrives on its friendly atmosphere, where neighbors become friends and local events foster a strong sense of belonging. Rollingwood is strategically located near top-rated schools, shopping centers, and recreational facilities, making daily life both convenient and enjoyable. Whether you're taking a leisurely stroll through the tree-lined streets or enjoying a weekend barbecue at one of the nearby parks, you'll find that Rollingwood is a place where memories are made.

With homes for sale in this enchanting subdivision, now is the perfect time to discover the lifestyle that awaits you in Rollingwood. Embrace the opportunity to become part of this vibrant community and experience the warmth and charm that makes Rollingwood truly special. Your dream home is just a visit away!

Newest Rollingwood Homes for Sale

$495,000
4 Beds ⋅ 2 Baths
Welcome home to this spacious and thoughtfully updated property offering a flexible floor plan, generous living spaces, and years of valuable improvements already completed! The heart of the home is the beautifully renovated 2025 kitchen, featuring crisp white cabinetry, sleek countertops, stainless steel appliances, recessed lighting, and a large center island that opens seamlessly to the surrounding living areas. One of the home's standout features is the expansive rear family room/sunroom, filled with natural light from walls of windows and offering plenty of space for entertaining, relaxing, or gathering around the fireplace. Adding even more versatility is a small in-law suite with its own kitchen, perfect for extended family, guests, or additional flexible living space. The home has benefited from numerous major improvements over the years, including a new roof (2015), new A/C and furnace (2016), upper siding, soffit and downspouts replaced (2024), exterior painting (2024), renovated main kitchen (2025), new dishwasher in the in-law suite (2025), A/C pump replacement (2026), and new front windows along with replacement of clouded windows in the rear room (2026). Outside, the spacious yard offers plenty of room to relax, garden, play, or entertain. With its combination of updated systems, refreshed finishes, flexible living space, and plenty of room to spread out, this home is ready for its next chapter. Life is great in 21228-come see why!

9 N Hilltop Rd, Catonsville

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033
$585,000
4 Beds ⋅ 3 Baths
Coming Soon!

1909 Tadcaster Rd, Catonsville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$2,495,000
6 Beds ⋅ 5 Baths
Not often does the combination of traditional design with modern updates come together as they have at 3405 Leland Street, a beautifully renovated 6 bedroom, 4.5 bath home in the highly sought after Rollingwood neighborhood of Chevy Chase. Recently updated with a gourmet kitchen, renovated baths and numerous thoughtful design touches throughout, the home blends modern comfort with inviting, spacious living. The main level is ideal for both everyday living and entertaining, with the gourmet kitchen offering direct access to the expansive rear flagstone patio, a breakfast room, a formal dining room, and welcoming living and family rooms, each with a fireplace, and a half bath. Upstairs, four bedrooms include a generous primary suite with an ensuite full bath, large walk-in closet, dressing table and washer and dryer, plus a second bedroom with its own ensuite full bath. The additional two bedrooms share a hall bath. The third level offers flexible space for another bedroom, office or workout area with additional storage. The lower level includes exceptional flexibility with a two car garage, recreation room with fireplace, additional bedroom and full bath, laundry, and storage. Outside, the large wraparound patio creates an ideal setting for outdoor dining, entertaining, or a private retreat. With its thoughtful updates, generous living spaces, multiple fireplaces, and prime Rollingwood location near Rock Creek Park and downtown Bethesda, 3405 Leland Street offers the perfect combination of style, comfort, and convenience.

3405 Leland St, Chevy Chase

Listing courtesy of Washington Fine Properties. Contact: info@wfp.com
$1,250,000
4 Beds ⋅ 5 Baths
Welcome to 7708 Tanner Robert Ct, a stunning stone-front Colonial tucked away on desirable cut-del-sac in Springfield.Offering approximately 3,900+ square feet of beautifully finished living space, this spacious home combines classic elegance with thoughtful updates and exceptional functionality. The main level features beautiful updated flooring, a welcoming foyer, formal living and dining area, a private office, and a spacious family room designed for everyday living and entertaining. The Kitchen offers generous cabinet and counter space and opens to the main living areas for an inviting, connected floor plan. Upstairs, You'll find four spacious bedrooms, including a generous primary suite. Providing plenty of room for family and guest.The finished lower level adds tremendous versatility with a full bathroom and a stylish wet-bar Security cameras and audio system on the property does not convey . The existing carpet on bedrooms will be replaced .

7708 Tanner Robert Ct, Springfield

Listing courtesy of Vera's Realty Inc.. Contact:

$1,550,000
5 Beds ⋅ 4 Baths
Timeless Colonial charm meets modern functionality in coveted Rollingwood! This classic Colonial in Chevy Chase’s sought-after Rollingwood neighborhood was thoughtfully renovated in 2016 to preserve its original 1940’s character amid a major refresh. Inside, a gracious foyer with hardwood floors opens to a living room with a wood-burning fireplace, detailed molding, and built-ins. A butler’s pantry connects to the dining room and an updated kitchen that features granite countertops, stainless steel appliances, and an island peninsula. Other standout features on the main level? A guest bedroom with an en-suite bath, and a sunlit family room with walls of windows. The upstairs offers three bedrooms and two full baths, including a spacious primary suite with dressing area, generous closet space, and an en-suite bath—while a finished third level provides flexible space for a bedroom or playroom. Additionally, the lower level of this home includes a rec room with a substantive brick fireplace, full bath, laundry, and ample storage. There are plenty of places to gather and commune here, and also plenty of space for . . . space! Beyond the dense integrity inside of this home, there is also the luxury of the exterior, which includes a gated backyard with brick patio and a private, landscaped setting. A slate roof, two-car garage, and driveway parking for four rounds out this residence. Comfortably situated near Rock Creek Park, Brookville Road shops and dining, this private and timeless abode offers easy access to Bethesda, DC, I-270, and I-495. Also listed for rent MLS #MDMC2226840.

7215 Rollingwood Dr, Chevy Chase

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Start Your Search